
TY  - JOUR
A1  - Deady, LW 
T1  - A search for lone-pair interactions in forward and reverse Menschutkin reactions of some diaza heterocycles
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1981
VL  - 34
IS  - 1
SP  - 163
EP  - 170
KW  - 
UR  - https://doi.org/10.1071/CH9810163 
N2  - The rates of methylation (forward reaction) of phthalazine (1), 1,8-naphthyridine (2), 1,10-phenanthroline (3), and of some ring methyl derivatives are compared with the rates of demethylation of the corresponding N-methyl quaternary iodides. It was observed for (2), and especially for (3), that a nitrogen lone pair in place of a CH group (quinoline and 8-methylquinoline, respectively) aids the forward reaction but does not have a commensurate retarding effect on the reverse process. In contrast to (3), 2,2´-bipyridine showed behaviour typical of a-substituted pyridines. The introduction of a 2-methyl group into (3) had an appreciable rate-enhancing effect on methylation (at N 10) and this is interpreted as evidence for lone-pair cooperativity in the forward reaction. 
ER  -

